Dimethylformamide → HCID 57056602, compound

HRID 373510Notes

Reaction equation

HRID 373510 reaction equation
Cl[CH2:2][CH2:3][CH2:4][N:5]1[C:9](=[O:10])[C@:8]2([C:19]3[C:14](=[CH:15][CH:16]=[C:17]([F:20])[CH:18]=3)[O:13][C@H:12]([C:21]([NH2:23])=[O:22])[CH2:11]2)[NH:7][C:6]1=[O:24].[OH:25][CH:26]1[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1.C([O-])([O-])=O.[K+].[K+].CN(C)C=O>>[OH:25][CH:26]1[CH2:31][CH2:30][N:29]([CH2:2][CH2:3][CH2:4][N:5]2[C:9](=[O:10])[C@:8]3([C:19]4[C:14](=[CH:15][CH:16]=[C:17]([F:20])[CH:18]=4)[O:13][C@H:12]([C:21]([NH2:23])=[O:22])[CH2:11]3)[NH:7][C:6]2=[O:24])[CH2:28][CH2:27]1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 79341Piperidin-4-olHCID 57208423HCID 57208423, compound

Product 1

HCID 57056602HCID 57056602, compoundYield 91.5%

Conditions

Temperature
80 °C

Procedure

A mixture of (2S,4S)-1'-(3-chloropropyl)-6-fluoro-2',5'-dioxospiro[chroman-4,4'-imidazolidine]-2-carboxamide (Reference Example 2, 15.0 g, 42.2 mmol), 4-hydroxypiperidine (8.52 g, 84.4 mmol), K2CO3 (7.00 g, 50.7 mmol) and N,N-dimethylformamide (100 ml, 1.29 mol) was stirred for 5 hours at 80° C. After distilling off the solvent, the residue was chromatographed on silica gel, eluted with CH2Cl2 /MeOH/NEt2 (5/1/1), and recrystallized from AcOEt/MeOH to give prism crystals of the desired compound (16.2 g, 91.5%).

Workup

  1. distillationAfter distilling off the solvent
  2. customthe residue was chromatographed on silica gel
  3. washeluted with CH2Cl2 /MeOH/NEt2 (5/1/1)
  4. customrecrystallized from AcOEt/MeOH

Sources & evidence

ORD record
ord-be7592fbb2884e689ccf7acce96c0e01
Source dataset
uspto-grants-1992_11
Patent number
US05164391

Reaction notes

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